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Hydrogen Sulfide → methyl (5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]-propoxy}-1H-indol-1-yl)acetate

HRID 734418
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734418
[SH2:1].[C:2]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:17]=[CH:16]3)=[C:6]([CH2:29][CH2:30][CH3:31])[CH:5]=1)#[N:3].C(NCC)C>CN(C=O)C>[NH2:3][C:2]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:17]=[CH:16]3)=[C:6]([CH2:29][CH2:30][CH3:31])[CH:5]=1)=[S:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 402Hydrogen SulfideHCID 8021DiethylamineHCID 70971790methyl {5-[3-(4-cyano-2-propylphenoxy)propoxy]-1H-indol-1-yl}acetate

Produkt 1

HCID 57845462methyl (5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]-propoxy}-1H-indol-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Hydrogen sulfide was passed through a solution of methyl {5-[3-(4-cyano-2-propylphenoxy)propoxy]-1H-indol-1-yl}acetate (Example 51, 787 mg, 1.94 mmol) in DMF (15 mL) for 30 minutes at rt. Diethyl amine (0.3 mL, 2.90 mmol) was added, and the solution was heated to 70° C. for 3 h. The reaction mixture was cooled to rt, and the residual H2S was removed by passing argon through the reaction mixture for 30 minutes. The solvent was evaporated under reduced pressure and the residue was filtered through a plug of silica and washed with EtOAc. Concentration of solvent yielded a brown oil which was used in the next step without further purification. LC/MS m/z 441.2 (M+H)+; RT 3.35 min.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe residual H2S was removed
  3. customfor 30 minutes
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationthe residue was filtered through a plug of silica
  6. washwashed with EtOAc
  7. customConcentration of solvent yielded a brown oil which
  8. customwas used in the next step without further purification
  9. customRT 3.35 min.

Quellen und Nachweise

ORD-Eintrag
ord-55255b986b944a3d92e37d5b0e558f0d
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592361B2

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